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Issue 24, 2016
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Mechanistic studies on intramolecular C–H trifluoromethoxylation of (hetero)arenes via OCF3-migration

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Abstract

The one-pot two-step intramolecular aryl and heteroaryl C–H trifluoromethoxylation recently reported by our group has provided a general, scalable, and operationally simple approach to access a wide range of unprecedented and valuable OCF3-containing building blocks. Herein we describe our investigations to elucidate its reaction mechanism. Experimental data indicate that the O-trifluoromethylation of N-(hetero)aryl-N-hydroxylamine derivatives is a radical process, whereas the OCF3-migration step proceeds via a heterolytic cleavage of the N–OCF3 bond followed by rapid recombination of a short-lived ion pair. Computational studies further support the proposed ion pair reaction pathway for the OCF3-migration process. We hope that the current study would provide useful insights for the development of new transformations using versatile N-(hetero)aryl-N-hydroxylamine synthons.

Graphical abstract: Mechanistic studies on intramolecular C–H trifluoromethoxylation of (hetero)arenes via OCF3-migration

  • This article is part of the themed collection: New Talent
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Supplementary files

Article information


Submitted
16 Jan 2016
Accepted
23 Mar 2016
First published
23 Mar 2016

Org. Biomol. Chem., 2016,14, 5599-5605
Article type
Communication

Mechanistic studies on intramolecular C–H trifluoromethoxylation of (hetero)arenes via OCF3-migration

K. N. Lee, Z. Lei, C. A. Morales-Rivera, P. Liu and M. Ngai, Org. Biomol. Chem., 2016, 14, 5599
DOI: 10.1039/C6OB00132G

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